2-Methyl-2-thiopseudourea → HCID 178426535, compound

Participants

Reaction Steps

The compound 5-(3-aminopropyl)-5-methyl-2,4-imidazolidinedione hemisulfate (229 mg, 1 mmol) was dissolved in 0.418 N aqueous barium hydroxide (3.5 ml.) and S-methylisothiourea (153.1 mg, 1.1 mol) was added. The suspension was shaken at room temperature for 6 1/4 hours and 0.418 N aqueous barium hydroxide (1 ml.) was added, followed by another 0.5 ml. of the aforementioned barium hydroxide solution 18 hours later. After 4 hours, S-methylisothiourea (70 mg., 0.5 mmol) was added and shaking of the suspension was continued for 66 hours. At that time only traces of 5-(3-aminopropyl)-5-methyl-2,4-imidazolidinedione hemisulfate could be detected. Barium sulfate was filtered off and washed with water, filtrate and washings were applied to a column containing 5 ml. of sulfonated polystyrene ion exchange resin, the column was washed consecutively with water (50 ml.) 10% by volume aqueous pyridine (25 ml.) and 2.5 M aqueous ammonium hydroxide solution (25 ml). Concentration of the ammoniacal effluent gave a colorless syrup from which crystalline 5-(3-[(aminoiminomethyl) amino]propyl)-5-methyl-2,4-imidazolidinedione was deposited on standing (207 mg., 0.97 mmol, 97%). Recrystallization from water afforded 5-(3-[(amino-iminomethyl)amino]propyl)-5-methyl-2,4-imidazolidienedione as fine needles, m.p. 294°-295° C.

Provenance & Evidence